Episodes

  • Episode 189: Connecting the Dots in Tech Leadership with Aleksandra Gjinovska

    Episode 189: Connecting the Dots in Tech Leadership with Aleksandra Gjinovska
    Sep 9 2025
    Aleksandra Gjinovska, Head of Technology at IT Labs, sat down with our host TC Gill for our podcast CTO Confessions to share her journey as a woman leading in a male-dominated industry and how mentorship, saying no, and organizational support shape future leaders. Whether you’re scaling teams, mentoring future leaders, or striving to foster inclusive leadership, this conversation is full of insights that will inspire and challenge you.
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    48 mins
  • Episode 188: Wealth Management Driven by Technology with Naresh Singh

    Episode 188: Wealth Management Driven by Technology with Naresh Singh
    Sep 2 2025
    Naresh Singh, Partner and CTO at Lenox Advisors, sat down with our host TC Gill for our podcast CTO Confessions to discuss how technology is reshaping wealth management from AI-driven data systems to leadership grounded in both technical foresight and servant leadership. Whether you’re navigating financial services, driving transformation through technology, or leading high-performing teams, this conversation will inspire and equip you with practical insights.
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    44 mins
  • Episode 187: Programmers' Resistance in the Age of AI with Allen Cheung

    Episode 187: Programmers' Resistance in the Age of AI with Allen Cheung
    Aug 26 2025
    Allen Cheung, SVP of Engineering at UJET.cx, sat down with our host TC Gill for our podcast CTO Confessions to explore how AI is reshaping the tech industry and why some programmers resist this transformation. Whether you’re building teams, navigating the shift to AI-powered engineering, or simply looking to embrace growth through change, this conversation will challenge and inspire you.
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    53 mins
  • Episode 186: Lessons from the Marines and Tech with Bob Hackney

    Episode 186: Lessons from the Marines and Tech with Bob Hackney
    Aug 12 2025
    What can the Marines teach us about leading high-performing tech teams? A lot more than you might think. In this episode, Bob Hackney, CTO at PerfectServe, shares how a mission-first mindset translates from the battlefield to the boardroom, delivering results without sacrificing your people. His “double win” approach is all about achieving objectives while growing and empowering teams. Whether you’re scaling a tech org, running global teams, or simply looking to lead with empathy and impact, this conversation will challenge and inspire you.
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    50 mins
  • Episode 185: Leading at the Intersection of Technology and Finance with Reinaldo Ynchaustegui

    Episode 185: Leading at the Intersection of Technology and Finance with Reinaldo Ynchaustegui
    Aug 5 2025
    In this episode of CTO Confessions, we sit down with Reinaldo Ynchaustegui, CTO in the asset management space, for an overview of what it really takes to lead in tech. From dissecting how to automate a tech team’s workflow without losing the human touch to exploring the critical role of emotional intelligence in leadership, Reinaldo shares insights from the frontlines. Tune in to hear the realities behind the role and the balance between tech and people.
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    54 mins
  • Episode 184: Do Good Leaders Get to the Top? A Discussion with Wes Bailey

    Episode 184: Do Good Leaders Get to the Top? A Discussion with Wes Bailey
    Jul 29 2025
    Can good leadership be taught or does it come down to who you are? In this episode, we sit down with Wes Bailey, Founder at Par Not Far, for a refreshingly honest conversation about leadership, bureaucracy, and why some of today’s sacred practices might need to go. If you’re tired of corporate speak and want something real, this is the episode for you.
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    1 hr and 3 mins
  • Episode 183: An AI Give-and-Take with Joel Krooswyk

    Episode 183: An AI Give-and-Take with Joel Krooswyk
    Jul 22 2025
    How can we separate real innovation from hype? In this episode, Joel Krooswyk, Federal CTO at GitLab, joins TC Gill for a thoughtful deep dive into the evolving role of AI in development, hiring, and leadership. Joel brings 25+ years of experience across private and public sectors and this conversation hits that perfect balance of vision and pragmatism. Tune in now and explore the full story!
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    48 mins
  • Episode 182: A CTO's Career Guide: Blending Tech and Business with James Long

    Episode 182: A CTO's Career Guide: Blending Tech and Business with James Long
    Jul 15 2025
    What happens when deep technical knowledge meets real-world domain expertise? In this episode, TC Gill is joined by James Long, CTO at Palomar, to explore what it takes to lead with clarity in a high-stakes environment. From modeling risk to building strong, cross-functional teams, this conversation is packed with practical insights for tech leaders. If you're looking to sharpen your leadership edge, this episode delivers.
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    1 hr and 12 mins